In his spare time, he continues to develop experimental games including The Marriage, Stars Over Half Moon Bay and Last Thoughts of the Aurochs.

On 7 October 2008, a press release noted that Electronic Arts Inc. had promoted Humble to Executive Vice President and Head of The Sims Label of EA. In this role, Humble was to be responsible for The Sims Label, the developer and marketer of life-simulation games and online communities with an emphasis on creativity, community and humor. The Sims is the best-selling PC franchise of all time.

An NPC (non-player character) in The Sims 2 expansion pack, FreeTime, is based on Humble. He is seen delivering a gift to new home-owners, the gift always being a computer, the computer having a sneak preview of The Sims 3.

On 23 December 2010, Linden Lab, the creators and operators of the virtual worldSecond Life, announced that he would become their new CEO as of January 2011. On 24 January 2014, Humble announced on his Facebook account that he would be leaving Linden Lab to pursue founding a new company that will "make Art, Entertainment and unusual things!". On 29 January 2015, Humble announced his latest solo project Cults & Daggers, with his new company Chaphat.